Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1198-1209.DOI: 10.6023/cjoc202110042 Previous Articles Next Articles
ARTICLES
张玉荣a,b, 王晗a,*(), 茆勇军a, 施世良a,b,*(
)
收稿日期:
2021-10-29
修回日期:
2021-11-28
发布日期:
2021-12-02
通讯作者:
王晗, 施世良
基金资助:
Yurong Zhanga,b, Han Wanga(), Yongjun Maoa, Shiliang Shia,b(
)
Received:
2021-10-29
Revised:
2021-11-28
Published:
2021-12-02
Contact:
Han Wang, Shiliang Shi
Supported by:
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Yurong Zhang, Han Wang, Yongjun Mao, Shiliang Shi. Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1198-1209.
[1] |
(a) Nugent, T. C. Chiral Amine Synthesis: Methods, Developments and Applications, Wiley-VCH, Weinheim, 2010.
|
(b) Lawrence, S. A. Amines: Synthesis, Properties and Applications, Cambridge University Press, Cambridge, U. K., 2004.
|
|
(c) Puentes, C. O.; Kouznetsov, V. J. J. Heterocycl. Chem. 2002, 39, 595.
|
|
[2] |
(a) Yus, M.; Gonzalez-Gomez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774.
doi: 10.1021/cr1004474 |
(b) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2013, 113, 5595.
doi: 10.1021/cr400008h |
|
(c) Huo, H.-X.; Duvall, J. R.; Huang, M.-Y.; Hong, R. Org. Chem. Front. 2014, 1, 303.
doi: 10.1039/C3QO00081H |
|
[3] |
(a) Dahlmann, M.; Grub, J.; Löser, E. Butadiene, Wiley-VCH, Weinheim, Germany, 2011.
|
(b) Weitz, H. M.; Löser, E. Isoprene, Wiley-VCH, Weinheim, Germany, 2000.
|
|
[4] |
(a) Wu, Z.; Zhang, W. Chin. J. Org. Chem. 2017, 37, 2250. (in Chinese)
doi: 10.6023/cjoc201704031 |
( 吴正兴, 张万斌, 有机化学, 2017, 37, 2250.)
|
|
(b) Xiong, Y.; Sun, Y.-W.; Zhang, G.-Z. Tetrahedron Lett. 2018, 59, 347.
doi: 10.1016/j.tetlet.2017.12.059 |
|
(c) Holmes, M.; Schwartz, L. A.; Krische, M. J. Chem. Rev. 2018, 118, 6026.
doi: 10.1021/acs.chemrev.8b00213 |
|
(d) Wang, P.-S.; Shen, M.-L.; Gong, L.-Z. Synthesis 2018, 50, 956.
doi: 10.1055/s-0036-1590986 |
|
(e) Perry, G. J. P.; Jia, T.; Procter, D. J. ACS Catal. 2020, 10, 1485.
doi: 10.1021/acscatal.9b04767 |
|
(f) Wang, X.-X.; Lu, X.; Li, Y.; Wang, J.-W.; Fu, Y. Sci. China Chem. 2020, 63, 1586.
doi: 10.1007/s11426-020-9838-x |
|
(g) Zhang, H.; Gu, Q.; You, S.; Chin. J. Org. Chem. 2019, 39, 15. (in Chinese)
|
|
( 张慧君, 顾庆, 游书力, 有机化学, 2019, 39, 15.)
|
|
[5] |
Kimura, M.; Miyachi, A.; Kojima, K.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2004, 126, 14360.
doi: 10.1021/ja0450354 |
[6] |
(a) Chen, T.-Y.; Tsutsumi, R.; Montgomery, T. P.; Volchkov, I.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 1798.
doi: 10.1021/ja5130258 |
(b) Schmitt, D. C.; Lee, J.; Dechert-Schmitt, A.-M. R.; Yamaguchi, E.; Krische, M. J. Chem. Commun. 2013, 49, 6096.
doi: 10.1039/c3cc43463j |
|
(c) Zhu, S.; Lu, X.; Luo, Y.; Zhang, W.; Jiang, H.; Yan, M.; Zeng, W. Org. Lett. 2013, 15, 1440.
doi: 10.1021/ol4006079 |
|
[7] |
(a) Li, C.; Liu, R.-Y.; Jesikiewicz, L. T.; Yang, Y.; Liu, P.; Buchwald, S. L. J. Am. Chem. Soc. 2019, 141, 5062.
doi: 10.1021/jacs.9b01784 |
(b) Jiang, L.; Cao, P.; Wang, M.; Chen, B.; Wang, B.; Liao, J. Angew. Chem., nt. Ed. 2016, 55, 13854.
|
|
(c) Li, M.; Wang, J.; Meng, F. Org. Lett. 2018, 20, 7288.
doi: 10.1021/acs.orglett.8b03216 |
|
(d) Fu, B.; Yuan, X.; Li, Y.; Wang, Y.; Zhang, Q.; Xiong, T.; Zhang, Q. Org. Lett. 2019, 21, 3576.
doi: 10.1021/acs.orglett.9b00979 |
|
(e) Gui, Y.-Y.; Hu, N.; Chen, X.-W.; Liao, L.-L.; Ju, T.; Ye, J.-H.; Zhang, Z.; Li, J.; Yu, D.-G. J. Am. Chem. Soc. 2017, 139, 17011.
doi: 10.1021/jacs.7b10149 |
|
[8] |
(a) Kojima, K.; Kimura, M.; Tamaru, Y. Chem. Commun. 2005, 4717.
|
(b) Kimura, M.; Kojima, K.; Tatsuyama, Y.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 6332.
doi: 10.1021/ja0616332 |
|
(c) Kimura, M.; Tatsuyama, Y.; Kojima, K.; Tamaru, Y. Org. Lett. 2007, 9, 1871.
doi: 10.1021/ol0703480 |
|
[9] |
Li, Y.-Q.; Shi, S.-L. Organometallics 2021, 40, 2345.
doi: 10.1021/acs.organomet.1c00096 |
[10] |
(a) McCammant, M. S.; Liao, L.; Sigman, M. S. J. Am. Chem. Soc. 2013, 135, 4167.
doi: 10.1021/ja3110544 pmid: 31857484 |
(b) Tao, Z.-L.; Adili, A.; Shen, H.-C.; Han, Z.-Y.; Gong, L.-Z. Angew. Chem. Int. Ed. 2016, 55, 4322.
doi: 10.1002/anie.201600148 pmid: 31857484 |
|
(c) Tortajada, A.; Ninokata, R.; Martin, R. J. Am. Chem. Soc. 2018, 140, 2050.
doi: 10.1021/jacs.7b13220 pmid: 31857484 |
|
(d) Boerth, J. A.; Maity, S.; Williams, S. K.; Mercado, B. Q.; Ellman, J. A. Nat. Catal. 2018, 1, 673.
doi: 10.1038/s41929-018-0123-4 pmid: 31857484 |
|
(e) Xiong, Y.; Zhang, G. J. Am. Chem. Soc. 2018, 140, 2735.
doi: 10.1021/jacs.7b12760 pmid: 31857484 |
|
(f) Yang, J.; Ji, D.-W.; Hu, Y.-C.; Min, X.-T.; Zhou, X.; Chen, Q.-A. Chem. Sci. 2019, 10, 9560.
doi: 10.1039/c9sc03747k pmid: 31857484 |
|
(g) Yang, J.; Liu, J.; Neumann, H.; Franke, R.; Jackstell, R.; Beller, M. Science 2019, 366, 1514.
doi: 10.1126/science.aaz1293 pmid: 31857484 |
|
(h) Li, Y.-Q.; Chen, G.; Shi, S.-L. Org. Lett. 2021, 23, 2571.
doi: 10.1021/acs.orglett.1c00488 pmid: 31857484 |
|
[11] |
(a) Denmark, S. E.; Guagnano, V.; Dixon, J. A.; Stolle, A. J. Org. Chem. 1997, 62, 4610.
doi: 10.1021/jo970686m |
(b) Lin, H.-C.; Wang, P.-S.; Tao, Z.-L.; Chen, Y.-G.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2016, 138, 14354.
doi: 10.1021/jacs.6b08236 |
|
(c) Fan, L.-F.; Luo, S.-W.; Chen, S.-S.; Wang, T.-C.; Wang, P.-S.; Gong, L.-Z. Angew. Chem., nt. Ed. 2019, 58, 16806.
|
|
[12] |
(a) Shinohara, Y.; Kudo, F.; Eguchit, T. J. Am. Chem. Soc. 2011, 133, 18134.
doi: 10.1021/ja208927r pmid: 22010945 |
(b) Tang, W.; Prusov, E. V. Angew. Chem., nt. Ed. 2012, 51, 3401.
pmid: 22010945 |
|
(c) Winter, P.; Hiller, W.; Christmann, M. Angew. Chem., nt. Ed. 2012, 51, 3396.
pmid: 22010945 |
|
[13] |
(a) Lian, X.; Chen, W.; Dang, L.; Li, Y.; Ho, C.-Y. Angew. Chem., nt. Ed. 2017, 56, 9048.
|
(b) Jing, S.-M.; Balasanthiran, V.; Pagar, V.; Gallucci, J. C.; RajanBabu, T.-V. J. Am. Chem. Soc. 2017, 139, 18034.
doi: 10.1021/jacs.7b10055 |
|
(c) Schmidt, V.-A.; Kennedy, C.-R.; Bezdek, M.-J.; Chirik, P.-J. J. Am. Chem. Soc. 2018, 140, 3443.
doi: 10.1021/jacs.8b00245 |
|
(d) Bohn, M.-A.; Schmidt, A.; Hilt, G.; Dindaroğlu, M.; Schmalz, H.-G. Angew. Chem., nt. Ed. 2011, 50, 9689.
|
|
[14] |
(a) Kimura, M.; Ezoe, A.; Mori, M.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 201.
doi: 10.1021/ja0469030 |
(b) Li, Y.-Q.; Shi, S.-L. Chin. J. Org. Chem. 2021, 41, 1939. (in Chinese)
|
|
( 李雨青, 施世良, 有机化学, 2021, 41, 1939.)
|
|
[15] |
(a) McCammant, M.-S.; Liao, L.; Sigman, M.-S. J. Am. Chem. Soc. 2013, 135, 4167.
doi: 10.1021/ja3110544 pmid: 25705367 |
(b) McCammant, M.-S.; Sigman, M.-S. Chem. Sci. 2015, 6, 1355.
pmid: 25705367 |
|
(c) Wang, C.-G.; Zhang, Y.; Wang, S.; Chen, B.; Li, Y.; Gao, Y.; Hu, P.; Wang, B.-Q.; Cao, P. Org. Lett. 2021, 23, 535.
doi: 10.1021/acs.orglett.0c04059 pmid: 25705367 |
|
(d) Pang, X.; Zhao, Z.-Z.; Wei, X.-X.; Qi, L.; Xu, G.-L.; Duan, J.; Liu, X.-Y.; Shu, X.-Z. J. Am. Chem. Soc. 2021, 143, 4536.
doi: 10.1021/jacs.1c00142 pmid: 25705367 |
|
[16] |
(a) Bin, H.-Y.; Wei, X.; Zi, J.; Zuo, Y.-J.; Wang, T.-C.; Zhong, C.-M. ACS Catal. 2015, 5, 6670.
doi: 10.1021/acscatal.5b01441 |
(b) Xu, G.; Zhao, H.; Fu, B.; Cang, A.; Zhang, G.; Zhang, Q.; Xiong, T.; Zhang, Q. Angew. Chem., nt. Ed. 2017, 56, 13130.
|
|
(c) Song, F.; Wang, F.; Guo, L. Feng, X.; Zhang, Y.; Chu, L. Angew. Chem., nt. Ed. 2020, 59, 177.
|
|
(d) Ma, W.-Y.; Han, G.-Y.; Kang, S.-l.; Pang, X.-B.; Liu, X.-Y.; Shu, X.-Z. J. Am. Chem. Soc. 2021, 143, 15930.
doi: 10.1021/jacs.1c08695 |
|
[17] |
(a) Montgomery, L. Angew. Chem., nt. Ed. 2004, 43, 3890.
|
(b) Standley, E.-A.; Tasker, S.-Z.; Jensen, K.-L.; Jamison, T.-F. Acc. Chem. Res. 2015, 48, 1503.
doi: 10.1021/acs.accounts.5b00064 |
|
(c) Hoshimoto, Y.; Ohashi, M.; Ogoshi, S. Acc. Chem. Res. 2015, 48, 1746.
doi: 10.1021/acs.accounts.5b00061 |
|
[18] |
(a) Lennox, A.-J.; Lloyd-Jones, G.-C. Angew. Chem., nt. Ed. 2013, 52, 7362.
pmid: 27081068 |
(b) Carrow, B.-P.; Hartwig, J.-F. J. Am. Chem. Soc. 2011, 133, 2116.
doi: 10.1021/ja1108326 pmid: 27081068 |
|
(c) Thomas, A.-A.; Denmark, S.-E. Science 2016, 352, 329.
doi: 10.1126/science.aad6981 pmid: 27081068 |
|
(d) Malapit, C. A.; Bour, J. R.; Brigham, C. E.; Sanford, M. S. Nature 2018, 563, 100.
doi: 10.1038/s41586-018-0628-7 pmid: 27081068 |
|
[19] |
Kimura, M.; Matsuo, S.; Shibata, K.; Tamaru, Y. Angew. Chem., nt. Ed. 1999, 38, 3386.
|
[20] |
(a) Zhang, W.-B.; Yang, X.-T.; Ma, J.-B.; Su, Z.-M.; Shi, S.-L. J. Am. Chem. Soc. 2019, 141, 5628.
doi: 10.1021/jacs.9b00931 |
(b) Cai, Y.; Zhang, J.-W.; Li, F.; Liu, J.-M.; Shi, S.-L. ACS Catal. 2019, 9, 1.
doi: 10.1021/acscatal.8b04198 |
|
(c) Cai, Y.; Ye, X.; Liu, S.; Shi, S.-L. Angew. Chem., nt. Ed. 2019, 58, 13433.
|
|
(d) Shen, D.; Zhang, W.-B.; Li, Z.; Shi, S.-L.; Xu, Y. Adv. Synth. Catal. 2020, 362, 1125.
doi: 10.1002/adsc.201901582 |
|
(e) Li, Y.-Q.; Li, F.; Shi, S.-L. Chin. J. Chem. 2020, 38, 1035.
doi: 10.1002/cjoc.202000019 |
|
(f) Cai, Y.; Ruan, L.-X.; A. Rahman; Shi, S.-L. Angew. Chem., nt. Ed. 2021, 60, 5262.
|
|
(g) Wang, Z.-C.; Gao, J.; Cai, Y.; Ye, X.; Shi, S.-L. CCS Chem. 2021, 3, 1445.
doi: 10.31635/ccschem.020.202000356 |
|
(h) Wang, Z.-C.; Xie, P.-P.; Xu, Y.; Hong, X.; Shi, S.-L. Angew. Chem., nt. Ed. 2021, 60, 16077.
|
|
(i) Cai, Y.; Shi, S.-L. J. Am. Chem. Soc. 2021, 143, 11963.
doi: 10.1021/jacs.1c06614 |
|
(j) Zhang, W.-B.; Chen, G.; Shi, S.-L. J. Am. Chem. Soc. 2021, 2022, 144, 130.
doi: 10.1021/jacs.1c12625 |
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